EP3098268B1 - Compound, coloring composition, inkjet recording ink, inkjet recording method, inkjet printer cartridge, inkjet recorded material, color filter, color toner, and transfer ink - Google Patents
Compound, coloring composition, inkjet recording ink, inkjet recording method, inkjet printer cartridge, inkjet recorded material, color filter, color toner, and transfer ink Download PDFInfo
- Publication number
- EP3098268B1 EP3098268B1 EP15735297.2A EP15735297A EP3098268B1 EP 3098268 B1 EP3098268 B1 EP 3098268B1 EP 15735297 A EP15735297 A EP 15735297A EP 3098268 B1 EP3098268 B1 EP 3098268B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- substituted
- unsubstituted
- ink
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims description 200
- 238000000034 method Methods 0.000 title claims description 53
- 239000000203 mixture Substances 0.000 title claims description 39
- 238000004040 coloring Methods 0.000 title claims description 28
- 238000012546 transfer Methods 0.000 title claims description 28
- 239000000463 material Substances 0.000 title claims description 25
- -1 carbamoyloxy group Chemical group 0.000 claims description 160
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 18
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
- 125000004986 diarylamino group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000004149 thio group Chemical group *S* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
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- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 239000000976 ink Substances 0.000 description 192
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
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- 239000003795 chemical substances by application Substances 0.000 description 43
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- 239000013078 crystal Substances 0.000 description 36
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- 238000003786 synthesis reaction Methods 0.000 description 32
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 23
- 239000000049 pigment Substances 0.000 description 22
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 18
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- 239000000654 additive Substances 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 15
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
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- 125000000962 organic group Chemical group 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000011160 research Methods 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 238000002360 preparation method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 0 CCNc1c(C)c(Nc(cc(c(C(c2ccccc2S(O)(=O)=O)=C2C[C@]3*C)c4)OC2=CC3=NC(C(C)C=C2*)C(*)=C2NCC)c4I*)c(C)cc1C Chemical compound CCNc1c(C)c(Nc(cc(c(C(c2ccccc2S(O)(=O)=O)=C2C[C@]3*C)c4)OC2=CC3=NC(C(C)C=C2*)C(*)=C2NCC)c4I*)c(C)cc1C 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 150000002989 phenols Chemical class 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0924—Dyes characterised by specific substituents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
Definitions
- alkenyl groups include a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, for example, a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group, and the like
- preferable cycloalkenyl groups include a substituted or unsubstituted cycloalkenyl group with 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from cycloalkene with 3 to 30 carbon atoms, for example, a 2-cyclopentene-1-yl group, a 2-cyclohexene-1-yl group, and the like
- bicycloalkenyl groups include a substituted or unsubstituted bicycloalkenyl group, preferably, a substituted or unsubstituted bicycloalkenyl group with 5 to 30 carbon atoms, that is, a monovalent group obtained by
- amino groups include an alkyl amino group, an aryl amino group, and a heterocyclic amino group
- preferable amino groups include a substituted or unsubstituted alkyl amino group with 1 to 30 carbon atoms, a substituted or unsubstituted anilino group with 6 to 30 carbon atoms, for example, a methyl amino group, a dimethyl amino group, an anilino group, an N-methyl-anilino group, a diphenyl amino group, a triazinyl amino group, and the like.
- alkyl or aryl sulfinyl groups include a substituted or unsubstituted alkylsulfinyl group with 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group with 6 to 30 carbon atoms, for example, a methylsulfinyl group, an ethylsulfinyl group, a phenylsulfinyl group, a p-methylphenylsulfinyl group, and the like.
- the compound which is represented by General Formula (1) has an amino group which has a specific substituent group.
- the action mechanism thereof is not clear; however, it is assumed that, the compound exhibits high saturation, excellent printing density, excellent lightfastness, and ozone resistance due to the compound having the kind of mechanism which is represented by General Formula (1).
- R 101 and R 102 represent a substituted or unsubstituted monoalkyl amino carbonyl group
- the monoalkyl amino carbonyl group is preferably represented by -CONHR 203 .
- R 203 represents an alkyl group with 1 to 12 carbon atoms, an alkyl group with 1 to 10 carbon atoms is preferable, an alkyl group with 1 to 6 carbon atoms is more preferable, a methyl group, an ethyl group, an isopropyl group, a hexyl group, a 2-ethylhexyl group, a dodecyl group, and a cyclohexyl group are even more preferable, and an isopropyl group is particularly preferable.
- R 101 and R 102 are preferably a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a carbamoyl group, a substituted or unsubstituted monoalkyl amino carbonyl group, a substituted or unsubstituted dialkyl amino carbonyl group, a substituted or unsubstituted monoaryl amino carbonyl group, or a substituted or unsubstituted diaryl amino carbonyl group, more preferably a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubsti
- Me represents a methyl group
- Et represents an ethyl group
- i-Pr represents an isopropyl group
- n-Bu represents an n-butyl group.
- the ratio of R and M is the molar ratio.
- the coloring composition of the present invention may contain other additive agents as necessary within a range which does not impair the effects of the present invention.
- additive agents include additive agents which may be used for the ink jet recording ink which will be described below.
- JP1993-148436A JP-H5-148436A
- JP1993-295312A JP-H5-295312A
- JP1995-97541A JP-H7-97541A
- JP1995-82515A JP-H7-82515A
- JP1995-118584A JP-H7-118584A
- JP1999-286637A JP-H11-286637A
- JP2000-87539 other than the patents described above, and use is also possible for the preparation of the ink jet recording ink of the present invention.
- the viscosity of the ink jet recording ink of the present invention is preferably 30 mPa ⁇ s or less.
- the surface tension thereof is preferably 25 mN/m to 70 mNm. It is possible to adjust the viscosity and surface tension by adding various types of additive agents, for example, viscosity adjusting agents, surface tension adjusting agents, specific resistance adjusting agents, coating film adjusting agents, ultraviolet absorbers, antioxidants, fading inhibitors, antifungal agents, rust preventive agents, dispersing agents, and surfactants.
- the support body in the recording paper or recording film is formed of a chemical pulp such as LBKP, and NBKP, a mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMP, and CGP, or waste paper pulp such as DIP, and it is possible to use a support body which is produced using various types of apparatuses such as a fourdrinier paper machine or a cylinder paper machine after mixing additive agents such as pigments binders, sizing agents, fixing agents, cationic agents, and paper strengthening agents, which are known in the art as necessary.
- additive agents such as pigments binders, sizing agents, fixing agents, cationic agents, and paper strengthening agents, which are known in the art as necessary.
- the surfactant functions as a coating aiding agent, a peeling property improving agent, a slidability improving agent, or an antistatic agent.
- the surfactant is described in each of the publications of JP1987-173463A ( JP-S62-173463A ) and JP1987-183457A ( JP-S62-183457A ).
- An organic fluoro compound may be used instead of the surfactant.
- the organic fluoro compound is preferably hydrophobic.
- the organic fluoro compounds include a fluorine-based surfactant, an oil-form fluorine-based compound (for example, fluorine oil), and a solid-form fluorine compound resin (for example, a tetrafluoroethylene resin).
- a charge control agent may be added as necessary; however, a colorless charge control agent is preferable from the point of view of the color developing property. Examples thereof include quaternary ammonium salt structures, calixarene structure, or the like.
- non-coated carriers formed of only magnetic material particles such as iron or ferrite, or resin-coated carriers in which the magnetic material particle surfaces are coated by a resin or the like may be used.
- the average particle diameter of the carrier is preferably 30 ⁇ m to 150 ⁇ m in volume average particle diameter.
- Exemplified Compound (1-5) was dissolved in 30 mL of methanol and a reaction was carried out by adding 3.9 g of 2-ethylhexyl amine (produced by Wako Pure Chemical Industries, Ltd.) thereto at an internal temperature of 5°C to 10°C.
- the obtained reaction liquid was purified with column chromatography (filler: SEPHADEX LH-20 (produced by Pharmacia), developing solvent: water/methanol).
- Fig. 4 shows the 1 H-NMR spectrum of Exemplified Compound (1-55) in dimethyl sulfoxide-d6.
- Fig. 2 shows the absorption spectrum of Exemplified Compound (1-55) in a diluted aqueous solution. As shown in Fig. 2 , the maximum absorption wavelength of absorption spectrum of the Exemplified Compound (1-55) in the diluted aqueous solution was 529 nm and the molar absorption coefficient was 92800.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Optical Filters (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014003571 | 2014-01-10 | ||
JP2014082185 | 2014-04-11 | ||
JP2014167833 | 2014-08-20 | ||
JP2014266429A JP6170901B2 (ja) | 2014-01-10 | 2014-12-26 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、及び転写用インク |
PCT/JP2015/050187 WO2015105108A1 (ja) | 2014-01-10 | 2015-01-06 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、及び転写用インク |
Publications (3)
Publication Number | Publication Date |
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EP3098268A1 EP3098268A1 (en) | 2016-11-30 |
EP3098268A4 EP3098268A4 (en) | 2017-03-22 |
EP3098268B1 true EP3098268B1 (en) | 2018-12-05 |
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Application Number | Title | Priority Date | Filing Date |
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EP15735297.2A Active EP3098268B1 (en) | 2014-01-10 | 2015-01-06 | Compound, coloring composition, inkjet recording ink, inkjet recording method, inkjet printer cartridge, inkjet recorded material, color filter, color toner, and transfer ink |
Country Status (6)
Country | Link |
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US (1) | US9701839B2 (ja) |
EP (1) | EP3098268B1 (ja) |
JP (1) | JP6170901B2 (ja) |
CN (1) | CN105899620B (ja) |
TW (1) | TWI629270B (ja) |
WO (1) | WO2015105108A1 (ja) |
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JP6167124B2 (ja) * | 2014-03-27 | 2017-07-19 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、カラーフィルタ、カラートナー、及び転写用インク |
EP3162858A4 (en) * | 2014-06-24 | 2017-06-28 | FUJIFILM Corporation | Coloring composition for dyeing or textile printing, ink for inkjet textile printing, method for textile-printing fabric, and dyed or textile-printed fabric |
WO2016052687A1 (ja) * | 2014-09-30 | 2016-04-07 | 富士フイルム株式会社 | 着色組成物、インクジェット記録用インク、及びインクジェット記録方法 |
JP6393769B2 (ja) * | 2014-09-30 | 2018-09-19 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、転写用インク、及び捺染方法 |
JP2017066208A (ja) * | 2015-09-28 | 2017-04-06 | 富士フイルム株式会社 | 着色組成物、インクジェット用インク、布帛を捺染する方法、及び染色又は捺染された布帛 |
CN108699348B (zh) * | 2016-02-24 | 2021-03-12 | 富士胶片株式会社 | 着色组合物、喷墨记录用油墨、喷墨记录方法及喷墨打印机墨盒 |
CN108699350B (zh) * | 2016-02-24 | 2021-03-12 | 富士胶片株式会社 | 着色组合物、喷墨记录用油墨、喷墨记录方法及喷墨打印机墨盒 |
EP3421548B1 (en) * | 2016-02-24 | 2024-01-24 | FUJIFILM Corporation | Coloring composition, inkjet recording ink, inkjet recording method, and inkjet printer cartridge |
JPWO2017146070A1 (ja) * | 2016-02-25 | 2019-01-10 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、及びインクジェットプリンタカートリッジ |
JP6531058B2 (ja) * | 2016-03-28 | 2019-06-12 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、及びインクジェット記録物 |
JP6539611B2 (ja) * | 2016-03-29 | 2019-07-03 | 富士フイルム株式会社 | キサンテン化合物の製造方法 |
JP2017179089A (ja) * | 2016-03-29 | 2017-10-05 | 富士フイルム株式会社 | インクセット、インクカートリッジ、インクジェットプリンター、インクジェット記録方法、及び記録物 |
JP6728012B2 (ja) * | 2016-09-30 | 2020-07-22 | 富士フイルム株式会社 | 水溶液、インクジェット記録用インク、インクジェット記録用インクの製造方法、インクジェット記録方法、及びインクカートリッジ |
WO2018062044A1 (ja) * | 2016-09-30 | 2018-04-05 | 富士フイルム株式会社 | 着色組成物、インクジェット記録用インク、インクジェット記録方法、及びインクジェットプリンタカートリッジ |
EP3521377A4 (en) * | 2016-09-30 | 2019-10-02 | FUJIFILM Corporation | AQUEOUS SOLUTION, COLOR COMPOSITION, INK IRRIGATION INK INK, INK IRRIGATION METHOD AND INK CARTRIDGE |
WO2018143279A1 (ja) * | 2017-02-03 | 2018-08-09 | 富士フイルム株式会社 | 着色組成物、インクジェット記録用インク、インクジェット記録方法、及びインクジェットプリンタカートリッジ |
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2014
- 2014-12-26 JP JP2014266429A patent/JP6170901B2/ja active Active
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2015
- 2015-01-06 WO PCT/JP2015/050187 patent/WO2015105108A1/ja active Application Filing
- 2015-01-06 EP EP15735297.2A patent/EP3098268B1/en active Active
- 2015-01-06 CN CN201580004033.6A patent/CN105899620B/zh not_active Expired - Fee Related
- 2015-01-08 TW TW104100512A patent/TWI629270B/zh not_active IP Right Cessation
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EP3098268A1 (en) | 2016-11-30 |
WO2015105108A1 (ja) | 2015-07-16 |
EP3098268A4 (en) | 2017-03-22 |
CN105899620A (zh) | 2016-08-24 |
TW201529563A (zh) | 2015-08-01 |
TWI629270B (zh) | 2018-07-11 |
JP2016041801A (ja) | 2016-03-31 |
JP6170901B2 (ja) | 2017-07-26 |
US9701839B2 (en) | 2017-07-11 |
US20160312032A1 (en) | 2016-10-27 |
CN105899620B (zh) | 2018-12-21 |
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